Sodium Hydroxide → 2,6-Dimethoxybiphenyl-4-carboxylic acid

HRID 1470615Notes

Reaction equation

HRID 1470615 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([O:19][CH3:20])[CH:6]=1)=[O:4].[OH-].[Na+]>C1COCC1>[CH3:20][O:19][C:7]1[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[C:9]([O:11][CH3:12])[C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57930909Methyl 2,6-dimethoxybiphenyl-4-carboxylate

Product 1

HCID 167685332,6-Dimethoxybiphenyl-4-carboxylic acidYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dimethoxy-biphenyl-4-carboxylic acid methyl ester (0.9 g, 3.3 mmol) in 10% aq. THF, an aq. solution of 5 N NaOH (5 mL) was added and the reaction mixture was refluxed for 5 h. After the reaction is completed, THF was removed completely under the vacuum and acidified with an aq. solution of 50% HCl. The resulting precipitate was filtered and washed thoroughly with water and dried to obtain the title compound (0.6 g, 70.5%).

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. customTHF was removed completely under the vacuum
  3. filtrationThe resulting precipitate was filtered
  4. washwashed thoroughly with water
  5. customdried

Sources & evidence

ORD record
ord-475de636e6ed4d03819af5ae9de33212
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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